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Videos de Conceptos Relacionados

Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Sharpless Epoxidation02:57

Sharpless Epoxidation

The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

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Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
13:05

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids

Published on: June 28, 2019

Epoxidación enzimática secuencial involucrada en la biosíntesis del poliéter lasalocida.

Atsushi Minami1, Mayu Shimaya, Gaku Suzuki

  • 1Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.

Journal of the American Chemical Society
|April 18, 2012
PubMed
Resumen

Las monooxigenasas que contienen flavina (FMOs) catalizan la epoxidación enantioselectiva, un paso clave en la construcción de esqueletos de poliéteres como el lasalocid. Este estudio aclara el mecanismo enzimático de la biosíntesis de poliéteres.

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Área de la Ciencia:

  • La bioquímica es la bioquímica.
  • Química orgánica es la química orgánica.
  • Biología Molecular Biología Molecular

Sus antecedentes:

  • Los esqueletos de poliéteres son cruciales en productos naturales como los poliéteres ionóforos.
  • La epoxidación enantioselectiva y la apertura de epóxido regioselectivo son pasos sintéticos clave.
  • Las monooxigenasas que contienen flavina (FMOs) son enzimas potenciales para la oxidación en la biosíntesis de poliéteres.

Objetivo del estudio:

  • Para investigar el papel de Lsd18, un FMO, en la biosíntesis del poliéter lasalocida.
  • Comprender el mecanismo enzimático de la epoxidación enantioselectiva en la construcción de poliéteres.

Principales métodos:

  • Análisis in vivo e in vitro de la enzima Lsd18.
  • El uso de imitaciones de sustratos, incluidas las olefinas simples y los dienes truncados.
  • Caracterización de los productos de la epoxidación.

Principales resultados:

  • Lsd18 realiza la epoxidación enantioselectiva de una manera gradual.
  • La enzima produce mono- o bis-epoxidos de tipo natural.
  • Demostró la participación de los FMO en la biosíntesis del poliéter de lasalocida.

Conclusiones:

  • Lsd18, una monooxigenasa que contiene flavina, es crucial para la biosíntesis del lasalocida.
  • El estudio aclara la vía enzimática para la construcción de esqueletos de poliéter.
  • Proporciona información sobre el mecanismo de epoxidación enantioselectiva por etapas.